- Smith degradation of the O-antigenic polysaccharide of Salmonella Dakar: structural studies of the products
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Two different oligosaccharides were obtained from the Smith degradation of the O-polysaccharide isolated from the lipopolysaccharide of Salmonella Dakar. The structures of these oligosaccharides were investigated by chemical analysis, NMR spectroscopy and MALDI-TOF mass spectrometry. The following structures of these products were determined: α-d-GalpNAc-(1→4)-α-d-Quip3NAc-(1→3)-α-l-Rha p-(1→2)-threitol and {A figure is presented}. where Quip3NAc is 3-acetamido-3,6-dideoxyglucose. The reaction products confirmed the structure of the repeating unit of the Salmonella Dakar O-polysaccharide reported previously [Kumirska, J.; Szafranek, J.; Czerwicka, M.; Paszkiewicz, M.; Dziadziuszko, H.; Kunikowska, D.; Stepnowski, P. Carbohydr. Res. 2007, 342, 2138-2143].
- Kumirska, Jolanta,Szafranek, Janusz,Czerwicka, Malgorzata,Golebiowski, Marek,Paszkiewicz, Monika,Dziadziuszko, Halina,Kunikowska, Danuta,Stepnowski, Piotr
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p. 1120 - 1125
(2008/09/20)
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- 2-Acetamido-2-deoxyaldonolactones from sugar formazans
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A new approach towards simple aldonic acid derivatives starting from the corresponding aldoses via the 2-acetamido-2-deoxy formazans resulted in the synthesis of 2-acetamido-2-deoxy-D-galactono-1,4-lactone (8), and its 6-deoxy (11) and 6-azido-6-deoxy (14) analogues on treatment with trifluoroacetic acid.The five-membered ring structure of the lactones and that of the intermediate lactone phenylhydrazone (7) was proved by 1H and 13C NMR studies, including deuterium-induced differential isotope shift (DIS) measurements.With sodium borohydride, lactones 8 and 11 were converted into 2-acetamido-2-deoxy-D-galactitol (15) and its 6-deoxy analogue (17), respectively.
- Zsoldos-Mady, Virag,Pinter, Istvan,Neszmelyi, Andras,Messmer, Andras,Perczel, Andras
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- UNEXPECTED FORMATION OF 2-ACETAMIDO-2-DEOXY DERIVATIVES OF SUGAR FORMAZANS
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A novel method for the preparation of acyclic 2-acetamido-2-deoxy derivatives of sugars was provided by deacetylation of acetylated sugar formazans with ammonia.The stereochemistry of the new 2-acetamido-2-deoxy sugar formazans was established by authenti
- Messmer, A.,Pinter, I.,Zsoldos-Mady, V.,Neszmelyi, A.,Hegedues-Vajda, J.
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p. 393 - 402
(2007/10/02)
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